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- Title
Modular Access to Tetrasubstituted N−H Pyrroles by Catalytic 1,3‐Dipolar Cycloaddition of Azomethine Ylides and α,β‐Ynones.
- Authors
Huang, Qian; Li, Zi‐Han; Zhao, Zhen‐Ni; Chen, Bo‐Ting; He, Feng‐Kai; Huang, Yi‐Yong
- Abstract
The development of efficient synthetic strategies for the preparation of tetrasubstituted N−H pyrrole derivatives, especially in an environmentally benign fashion is important yet challenging. Herein, we report a copper(II)‐catalyzed tandem reaction involving 1,3‐dipolar cycloaddition of α,β‐ynones and glycine iminoesters, followed by copper(II)‐promoted oxidative (air) dehydrogenative aromatization, allowing de novo access to tetrasubstituted N−H pyrroles in up to 81 % yield under green reaction conditions. A possible reaction pathway is tentatively proposed. Finally, fully substituted pyrroles are available by N‐alkylation, and a preliminary phase‐transfer catalytic asymmetric N‐alkylation was also studied to give an axially chiral pyrrole.
- Subjects
CHIRALITY element; PYRROLES; COPPER; SCHIFF bases; YLIDES
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 30, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202400437